


Chapter 11.5, or: A Thorough Exploration of Destina [Sex 101 Timestamp]

by Anonymous



Series: Sex 101 Verse [2]
Category: Supernatural
Genre: Angst, BDSM, Bondage, Dirty Talk, Facials, Fluff, Multi, Pegging, Threesome - F/M/M, Timestamp, Voice Kink
Language: English
Status: Completed
Published: 2014-08-21
Updated: 2014-08-21
Packaged: 2018-02-14 02:25:17
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,834
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2174490
Author URL: https://archiveofourown.org/
Summary: <blockquote class="userstuff">
              <p>Cas nods, and stares down at Dean, holding his wrist tighter so that it burns a little more, just to keep him from reaching out and touching the beautiful being in front of him, leaning down and kissing him, taking him, doing everything Katarina just did to him and more; exploring the entire spectrum of sexuality with this man who is, essentially, sex personified.</p><p>***</p><p>Wherein Dean, Cas, and Katarina go for round two. [Set immediately following the events of chapter 11 of <i>Sex 101</i>]</p>
            </blockquote>





	Chapter 11.5, or: A Thorough Exploration of Destina [Sex 101 Timestamp]

**Author's Note:**

  * For [shiphitsthefan](https://archiveofourown.org/users/shiphitsthefan/gifts).



It takes Cas a solid minute for his breathing to get back to normal, and two more minutes after that for his heart rate to slow down.

Thankfully, in the interim, Dean unties Cas, and Cas brings his arms up to inspect the damage on his wrists. They're bright red and burn when he runs his hand over the welt that the rope leaves.

He hisses through his teeth, but it's not a bad pain. It actually makes his dick twitch— a bit uncomfortably and much too soon— when he presses his fingers a little harder against the marks.

Dean squats down in front of him. His eyes are bright, and his face and chest are flushed. A small smile creeps up his face as he sees Cas' curious inspection of his wrists. "Feels good, doesn't it?"

Cas nods, and stares down at Dean, holding his wrist tighter so that it burns a little more, just to keep him from reaching out and touching the beautiful being in front of him, leaning down and kissing him, taking him, doing everything Katarina just did to him and more; exploring the entire spectrum of sexuality with this man who is, essentially, sex personified.

Dean places a hand on Cas' knee, and Cas feels it through his pant leg, acutely aware of the heat coming off of each finger and his palm, burning a brand onto him that feels so much better than the ones on his wrists. Nodding toward the bathroom, Dean says, "Might wanna get cleaned up for round two."

Cas shakes his head in disbelief, eyes widening. "Round two? Dean, I can't do a round two."

Dean chuckles and stands, slipping the condom off of his waning dick and tying it off to toss in a trash can, as though it's a completely normal thing to be doing in front of one's best friend-slash-fake husband-slash-whatever they are nowadays, the status of which seems to change hourly.

"You don't understand, Dean," Cas begins, "this is going to _kill me_."

Dean's eyebrows shoot up into his forehead. "It's going to kill _you_? Dude, we all already came, do you know what that means round two is gonna even _be_?"

Before Cas can respond that he has no idea, but whatever it is, Cas simply _will not survive it_ , Katarina opens the bathroom door and glides back into the room, black curls bouncing on her shoulders, plush lips reddened from more than just makeup, Dean's bite marks scattered over her tan shoulders.

Cas makes the mistake of letting his gaze sweep over her body, which passes the beautiful curve of her breasts and waist and lands on an enormous black strap-on between her hips.

He looks over to Dean, who is staring at Katarina, somehow looking both terrified and bemused, and says, "Called it," then swallows audibly.

"Are you ready, _mi amor?"_ Katarina asks, striding over to Dean and caressing the side of his face, then stretches up on her toes to kiss Dean, sweet and chaste.

Cas looks between them, mouth agape, overcome with an emotion he's never felt. "I, uhh... I'll be right back." Cas stands and runs into the bathroom, closing the door behind him.

He's not jealous— well, maybe he's jealous. _Envious_ is a better term. He's wound tight even though he just came, but he just... _wants_. He wants what he can't touch, what he may never touch because of Dean's ridiculous, hypocritical notions of masculinity.

According to Dean, it's perfectly okay to strip in front of masses of people, have a long-standing dom, and sell his body for money, which includes having sex with men.

Yet despite all of that, having romantic feelings toward a man is still decidedly _not_ okay.

Well, Cas decides as he undresses himself, he can play this game too.

When he leaves the bathroom, Dean and Katarina are on the bed, legs entwined and kissing in a way Cas has never seen Dean kiss anyone before. He's usually reserved, calculated, controlling the kiss and every aspect of it.

This, though, makes Cas' head tilt. Dean's fingers are threaded in Katarina's hair, and she's devouring him, consuming him, biting his lower lip and pulling it with her teeth while smiling.

Another pang of envy runs through Cas' body, and he knows it's ugly and childish, to be given the opportunity to see this, which is _exactly what he asked for_ , while feeling jilted that he's not given more.

They don't look up as Cas approaches them, until Katarina, on top of Dean and lying between his legs, dips her head down and kisses his neck.

Dean opens his eyes and glances briefly at Cas, then does a double-take as he runs his gaze down Cas' naked body. He bites his bottom lip and groans, " _Damn_ , Cas. Why didn't you tell me that's what you had hiding under that goddamn trench coat all these years?"

Cas slides in bed next to them, not touching— he knows the rules— and propping his head up on his hand. "Why? It's not like you would have done anything about it."

Dean's face flickers with hurt for a moment before Katarina lifts her head and looks up and down Cas's body too. _"Mi amor_ ," she says to Dean, sultry and low, "it looks like your toy wants to play, too." She looks at Cas like he's prey, and his dick twitches again at her glare.

He may now understand Dean's appreciation of being constantly looked upon.

It's incredibly... _validating_. To be seen. To be admired. To be wanted.

She looks down at Dean and asks, "You are sure I am not allowed to have him?"

"He's mine, Kat," Dean replies, terse, one arm draped around her waist and the other above his head.

Katarina sighs. "This is unfair. But I understand, _mi amor_. You cannot touch him, so no one can."

"That's not—" Dean begins.

Katarina interrupts him by shoving her tongue in his mouth again. When she breaks the kiss, she reaches up and grabs the bottle of lube from the night stand, then uncaps the lid and coats her fingers with it. She whispers, "You do not owe me an explanation, _mi amor_. You do not need my absolution. You need your own."

Dean opens his mouth to reply, "But it's not—" then chokes on his words when Katarina reaches down and slips a finger into him.

She shushes him and watches his face as she slides her finger out and presses back in, earning a small whimper from Dean, whose eyes flutter closed.

Cas watches, enrapt, a foot away from them on the other side of the bed, taking in the undulating motions of Katarina's hands, the way Dean's skin flushes pink, how his lips part as he gasps out sighs of pleasure, squirming and writhing under Katarina's touch.

"Another," Dean whispers, voice cracking, "please, Mistress."

Katarina chuckles and slides in a second finger.

Dean lets out a low moan, and reaches out to take Cas' hand in his own.

Cas gasps at the sudden, affectionate gesture, the feel of Dean's hand squeezing his. He brings it to his mouth and turns it, then kisses Dean's wrist and down his forearm, and back up to his palm. He takes two of Dean's fingers in his mouth and sucks on them, swirls them around his tongue, tasting the salty sweetness of his skin, the ridges and calluses of his deft fingers.

Katarina turns her attention to Cas and smiles, devilish. "That mouth of yours will be the death of me, handsome man."

Cas glances up at her and smirks around Dean's fingers. His stomach does an excited flip at being approved by Katarina, and he decides he  _loves_ the way she looks at him.

He wants Dean to look at him like Katarina does.

Dean's hips twitch up with every thrust of her fingers into him, and he watches Cas take his fingers down his throat, touching the back of it and swallowing them.

 _"Fuck_ , Cas," Dean growls between clenched teeth. "Where'd you learn to do that?"

Cas' eyes narrow as he thinks, and he replies, "I probably spend too much time watching your mouth than is strictly necessary."

Dean opens his mouth to respond, but Katarina does something that makes Dean's back arch off the bed, and he cries out, _"Fuck!"_

"Always so sensitive," Katarina coos, slipping her fingers out and back in again, then holds them there and shifts in such a way that Dean wails again.

Cas furrows his brow, and remembers he read somewhere that a man's prostate is incredibly sensitive. He bites his lip to keep from asking if he can try.

Watching Dean pant and writhe and bite his lip, the flush from his chest creeping up to his cheeks, emphasizing the dusting of freckles across his face which Cas has spent countless hours mapping out in his mind, like constellations to be memorized, Cas is hard again, but this time his hands are free, so he touches himself as Dean slips another finger into his mouth.

"Ready," Dean chokes out, with a small nod.

Katarina slides her fingers out and sits up on her knees, reaching to the end of the bed to grab the lengths of rope. "Arms above your head, _puto_ ," she tells Dean with a swift slap to his thigh.

Dean meets Cas' gaze as he takes his fingers out of his mouth, and moves toward him, staring at his lips, before stopping himself and pausing, then bringing his finger up to his own mouth, tasting Cas' saliva on himself before lowering his gaze and lifting his arms above his head.

Katarina, swift and sure, ties each of Dean's knees to his elbows, then reaches up to bind his wrists together and secure them to the posts of the headboard.

Dean hisses as the ropes twist against his existing burns.

Cas's body _aches_ at the sight, Dean completely splayed open, dick hard and leaking a filthy white pool on his stomach, already writhing against his restraints, shifting himself to inch closer and closer to Katarina's strap-on, pleading with his eyes for Katarina to fuck him open.

 _Fuck_ , Cas thinks. _He's_ _such a filthy fucking cumslut._

Cas pauses his hand on his dick and it jolts into his palm. Did he just refer to Dean, _his_ Dean, as a 'filthy fucking cumslut' in his head? Isn't that degrading, humiliating, disrespectful?

It's in the scene, Cas reminds himself. It's okay in the scene, where anyone can safeword if necessary. This scene is the safest place to think these things, to push and test the boundaries, to fall and trust that Dean or Katarina will catch him.

And, Cas notes, Dean really _is_ a filthy fucking cumslut. Which is really, _really_ hot.

Katarina slicks the strap-on with lube and lines it up with Dean's entrance.

Cas gets an idea.

He shifts closer to Dean, still not touching, but close enough that he can feel Dean's body heat radiate toward him. Resting his head on the pillow next to him, Cas reaches up and runs his fingers through Dean's hair, trails them gently down his face, and leans in, grazing the shell of Dean's ear with his lips. Cas whispers, "You're such a filthy fucking cumslut, Dean," at the same time Katarina presses into him.

Dean shouts and arches off the bed again, dick leaping and pulsing, bright red with a pearl of cum at the tip which slowly rolls down the shaft as Katarina presses deeper into him.

 _"Fuck_ , Cas, your mouth is gonna be the death of me too." Dean's voice is utterly fucking _wrecked_ , and his body is trembling, bracing himself for Katarina to bottom out.

Cas glances up at Katarina, whose face is set in concentration, hands rubbing gentle circles up and down the backs of Dean's thighs. She looks at Cas momentarily and winks, then nods, urging him on.

"Yeah?" Cas whispers again, gaining a surge of confidence at Katarina's continued approval, lowering his hand to pump his own dick. "You wanna feel this mouth on you? Lips wrapped around your cock?"

At the word _cock_ , Katarina snaps her hips back into Dean, shoving the massive dildo all the way in him.

Dean cries out again, pulling at his restraints, eyes squeezed shut. He pants and nods as Katarina pulls out and shoves back into him again and again, speeding up her pace as she completely takes him apart.

"I'm sorry, Dean. I didn't hear you. Was that a yes that you want me to shove your dick in my mouth and swallow you down?" Cas asks, speeding up his fist on his own cock in time with Katarina's thrusts.

A bead of sweat trickles down Dean's forehead and Cas leans in to lick it off of him, then trail kisses down the side of his face and suck his earlobe between his teeth.

"Yeah," Dean replies, panting, voice breaking. "Cas, please... want you..."

When Cas breaks away, Dean turns his head and leans in to kiss him, but Cas backs off. " _Ah ah_ , Dean, your scene, your rules."

"I'm changing the rules," Dean bites out.

Cas shakes his head. This time when he speaks, his voice is rougher, quieter, small pants between each word as he fucks his fist, and replies, "No, too late now."

 _"Fuck,"_ Dean says, then screams, _"Fuck!"_ when Katarina angles her hips differently.

"You know, handsome man," she begins, "I used to play a game with my _puto_ here to see what it would take to make him come without touching him."

Small whimpers and moans escape from Dean's lips as she continues fucking into him.

"Did you ever get him to?" Cas asks.

She huffs a laugh. "Never. But with both of us? I think we can win the game."

Cas leans into Dean's ear again and whispers, "You like that idea, you fucking cocktease? You like the idea of wanting me to touch you so badly that you come just from _thinking_ about it? From thinking about my hand," Cas takes his hand off his dick and hovers it over Dean's, which bobs up to meet his palm, but Cas doesn't touch it, "jacking you off. From thinking about my mouth," Cas mouths light, open kisses up and down Dean's shoulder and neck, then back up to his ear, "taking you in and sucking you down." He touches himself again and gathers cum on his fingers, then lifts his hand to slide two fingers into Dean's mouth, "From thinking about me straddling you and fucking myself on your cock."

Dean trembles under his restraints and sucks Cas' fingers with abandon, lifting his head to take in as much as he can.

Cas lets out an involuntary moan at the feel of Dean's tongue rolling around his fingers, the idea of Dean tasting him and wanting more. He hisses, and says, "Such a dirty little slut, Dean. _Fuck_ , I want those lips around my cock."

Cas pulls his fingers out, then reaches down to pump himself a few more times, and shoves his fingers back into Dean's mouth.

Dean groans around Cas' fingers, and Katarina quickens her pace, fucking into Dean fast and hard. His occasional moans turn into constant streams of noise ranging from choked whines to shouts of pleasure when Katarina grazes his prostate.

Cas removes his fingers again and Dean pleads, "Please, Mistress, touch me." He looks at Cas, "Please, Cas. I need—" He's interrupted by his own cry of pleasure, eyes shutting and head rolling back onto the pillow as Katarina pounds continuously into him.

"I'm sorry, Dean, I can't touch you." Cas gets on his knees and straddles Dean's chest, then he leans down to place his head on his forearm, resting on the headboard. He looks down at Dean as he fists himself in his palm, inches from Dean's mouth. "But I can do this."

Dean lifts his head and opens his mouth, but Cas pulls away. "No touching, Dean. Your mistress wouldn't like you touching me if she's not allowed to either."

Dean whines and drops his head back to the pillow.

Cas's cock is hard and slicked with his own cum, and he watches Dean's face, etched in pleasure and torture, still writhing against his binds, eyes crossed as he stares at Cas' cock hovering above his mouth, lips open to take it in with a silent plea of want.

A fire burns in the pit of Cas's abdomen, a hot coil ready to spring at any moment.

This is exactly what Cas has always wanted: Dean, below him, desperate and wanting and coming apart, filthy fucking lips pleading for Cas' cock to be shoved between them, beautiful freckles and flushed cheeks begging for Cas' cum to coat them.

Cas looks back to Katarina, whose hand is under the strap-on, between her legs as she watches them, lower lip between her teeth and brown eyes darkened with lust.

She smiles when Cas looks at her, and says, "Come on his face, handsome man," while fucking into Dean even faster, rocking her hips upward with every thrust.

Dean's back arches off the bed again, and Cas's balls graze Dean's chest, which sends a shiver up his spine, wanting nothing more than to feel _more_ of Dean on him, in him, anywhere and everywhere. He wants to experience this with Dean, experience everything with him.

But right now, Cas is reveling in his small vengeance, watching Dean want him openly, eyes locked on Cas', mouth open wide to take what he's given.

Katarina's soft panting turns into broken moans.

Dean is beyond words, but manages to croak out, "Mistress, I'm gonna..."

"Yes, _mi amor_ ," Katarina exhales. "You may come."

Dean's breath stops as he stares into Cas' eyes, hovering at the brink of his orgasm, and Katarina shouts, shoving into Dean with erratic movements, then pushes upward into him once more.

Dean cries out, back lifting off the bed again and coming into contact, just barely, with Cas's dick, which is all it takes for Cas to pump himself in his fist one more time and come all over Dean's face with a choked sob as he watches Dean ride down the waves of his orgasm, white hot streaks falling onto his slicked red lips and flushed face. It rolls down his chin and onto his neck, gets tangled in his eyelashes and hair. His tongue darts out to lick it off his lips, and swallows down the cum that fell into his mouth, which makes Cas jolt with another intense wave of pleasure.

Their eyes meet for a moment, and reality hits Cas like a brick.

He just came. On Dean Winchester's _face_.

Half of him is terrified at the inevitable emotional fallout that's likely to commence from this. The other half of him is thrilled at how utterly fucking _hot_ Dean looks, underneath him, tied up, fucked-out, and covered in Cas' cum.

He collapses beside Dean, barely paying attention as Katarina slides out of him and takes off the strap-on, then climbs over Dean to untie the ropes.

Dean lets his limbs fall onto the bed, and Katarina gets up to wet a towel. When she comes back, she wipes Dean's face and neck and chest with it, murmuring, "So _good_ , _mi amor_. So good."

"Thank you, Mistress," Dean whispers, eyelids drooping.

When Katarina finishes cleaning him up, she leans down and whispers something in Dean's ear.

Dean smiles, and replies, "I will."

She smiles back and kisses him on the lips, gentle and languid.

This time when Cas watches it, he doesn't feel envy. He knows that what Dean and Katarina have is different than what Dean and Cas have, but no more or less important, just more physical.

For the moment, Cas is settled in the level of physical intimacy between he and Dean. For the moment, he can understand Dean's reservations.

Should that understanding ever dissipate, Cas will always have the memory of coming on Dean's face, which, if nothing else, should serve as adequate masturbatory fodder for the rest of his life.

When Katarina stands up, she caresses Dean's face, and he leans into the touch.

"I have to get back to my Gina now, but please keep in touch, _mi amor_. I do not want to go years without speaking to you or fucking you again."

Dean smiles up at her. "Sure thing, Kat. We'll meet up again soon."

"Good," she replies, then walks over to the other side of the bed to lean down and kiss Cas on the cheek. "It was lovely meeting you, handsome man. Be sure to treat my Dean well."

Cas' mind is too fuzzy for words, so he nods his agreement.

Katarina collects her items from around the room and stuffs them in her handbag, then dons her coat and hat. She stops at the door and calls, "Goodnight, _mis amores_ ," before leaving and shutting the door gently behind her.

Cas tentatively scoots closer to Dean and rests his head on his chest, arm draped across his abdomen, watching it rise and fall with Dean's breaths.

Dean wraps his arm around Cas' back and brings him in closer, pressing his cheek to the top of Cas' head.

After several moments of silence but for the steady, rhythmic beat of Dean's heart, Cas asks, "What did she say to you?"

Dean doesn't reply immediately, so Cas assumes he fell asleep, and closes his eyes to fall asleep too.

At last, Dean replies, voice barely above a whisper, _"'Don't forget to walk the line.'"_

"What does that mean?"

"[It's from a song](http://youtu.be/KHF9itPLUo4). It was something she always said to calm me down after scenes. Helped with the sub drop. It means that I should trust myself and my instincts, and that the line I'm walking will never lead my astray so long as it's my own path I'm following." Dean pauses before adding quietly, "It means I shouldn't be afraid."

Cas isn't sure how to respond, so instead, he asks, "Can you sing it?"

"I don't really sing," Dean replies.

Cas scoffs. "You sing in the car all the time."

Dean sighs, and says, "Fine, but only because it's short."

He clears his throat and begins:

_I keep a close watch on this heart of mine_  
_I keep my eyes wide open all the time_  
_I keep the ends out for the tie the binds_  
_Because you're mine_  
_I walk the line_

Like everything Dean refuses to admit, Cas finds Dean's singing voice as beautiful as his dancing. It's just further evidence that Dean himself is art, both the creator and creation of his own masterpiece.

Cas falls asleep in Dean's arms, listening to his deep voice reverberating through his chest, and wondering how he got so lucky to be given the opportunity to love this man, this art, with every fiber of his now-human being.


End file.
